On Water: Metal-Free Synthesis of Highly Functionalized Benzothiazolylidene from ortho-Haloanilines

Kapil Mohan Saini, Rakesh K. Saunthwal, Shiv Kumar, Akhilesh K. Verma*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

6 Citations (Scopus)

Abstract

An environmentally benign, transition-metal-free organic base promoted one-pot cascade synthesis of highly functionalized benzo[d]thiazol-2(3H)-ylidene benzamide in the presence of water was accomplished by three-component reaction of ortho-iodoanilines, acrylates, and aroyl isothiocyanates. The protocol involves the in situ generation of thiourea intermediate followed by triethylamine induced intramolecular SN Ar displacement reaction and subsequent Michael addition onto acrylate leads to the formation of benzo[d]thiazol-2(3H)-ylidene benzamide. Benzo[b]thiazole is also generated in good yields using amidation and intramolecular aromatic nucleophilic substitution chemistry. The control experiments support the proposed mechanistic pathway. Further X-ray crystallographic studies confirmed the assigned structures of the fused benzamide.

Original languageEnglish
Pages (from-to)2689-2698
Number of pages10
JournalJournal of Organic Chemistry
Volume84
Issue number5
Early online date31 Jan 2019
DOIs
Publication statusPublished - 1 Mar 2019

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